I agree with the comments made about Hill Street Blues and The Larry Sanders Show.
I'm not a Gary Shandling fan myself, but that show was about him being a complete dick and the supporting cast and writing were stellar, for the time. Those going back and watching it now may not enjoy it as much because so much has been done since. Same for Hill Street Blues. At the time, it and Cheers were the shows that had top notch writing and great characters.
I have only seen a few episodes of the Sopranos, and it is well done. At the time though, I was sick of the mob movies and shows, so my interest just wasn't there anymore.
I have missed so much TV. I haven't had a TV for about a decade, and the most recent show I have watched from beginning to end is Deadwood. HBO has come a long way.